TY - JOUR
T1 - Formal total synthesis of aspergillide A
AU - Izuchi, Yuko
AU - Kanomata, Nobuhiro
AU - Koshino, Hiroyuki
AU - Hongo, Yayoi
AU - Nakata, Tadashi
AU - Takahashi, Shunya
N1 - Funding Information:
This work was supported in part by the Chemical Genomics Project (RIKEN) and a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan.
PY - 2011/1/31
Y1 - 2011/1/31
N2 - The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.
AB - The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.
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U2 - 10.1016/j.tetasy.2011.01.016
DO - 10.1016/j.tetasy.2011.01.016
M3 - Article
AN - SCOPUS:79952488127
VL - 22
SP - 246
EP - 251
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 2
ER -